Issue 19, 2019

Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species

Abstract

A visible light-induced vicinal diazidation of various alkenes using stable sulfonium bis(acetoxy)iodate(I) and sodium azide as a radical precursor is described. The trimethylsulfonium [bis(azido)iodate(I)] species, intrinsically generated in situ, demonstrated unprecedented reactivity toward C[double bond, length as m-dash]C π bond-promoting selective azidation under photochemical conditions without any photoredox or metal catalyst. The visible-light stimulated diazidation reaction provides a convenient and straightforward approach to highly prevalent vicinal nitrogen scaffolds of myriad therapeutic importance.

Graphical abstract: Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species

Supplementary files

Article information

Article type
Communication
Submitted
01 jan 2019
Accepted
08 feb 2019
First published
11 feb 2019

Chem. Commun., 2019,55, 2833-2836

Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(I) species

T. R. Reddy, D. S. Rao and S. Kashyap, Chem. Commun., 2019, 55, 2833 DOI: 10.1039/C9CC00007K

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